2,4,4,5-Tetramethylcyclohex-2-en-1-one

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  • Identifiers

    CAS number
    78405-57-9

    Molecular formula
    C10H16O

    SMILES
    CC1CC(=O)C(=CC1(C)C)C

  • Odor profile

    Mint 68.57%
    Camphoreous 63.32%
    Herbal 60.9%
    Sweet 53.78%
    Woody 53.42%
    Tobacco 46.37%
    Spicy 39.52%
    Phenolic 37.92%
    Cooling 37.22%
    Hay 34.64%

    Scent© AI

  • Properties

    XLogP3-AA
    2.6

    Molecular weight
    152.23 g/mol

    Vapor pressure est.

    • hPa @ 20°C
    • hPa @ 25°C

    Evaporation rate
    Moderately fast

    Boiling point est.
    205°C

    Flash point est.
    75.76 ˚C

  • Applications

    2,4,4,5-Tetramethylcyclohex-2-en-1-one (CAS 78405-57-9) is a sterically congested cyclic enone used primarily as a synthetic intermediate across pharmaceuticals, agrochemicals, and fine chemicals; its activated enone handles Michael (1,4-) additions, Diels-Alder reactions, Robinson annulation, and selective hydrogenation/oxidation to build densely substituted cyclohexanones and to elaborate into terpene/ionone-type scaffolds for fragrance applications. At research scale, it serves as a model substrate to probe asymmetric catalysis, stereocontrol in 1,4-additions, and steric effects; after functionalization, it can deliver drug-like precursors, crop-protection intermediates, flavor and fragrance ingredients, or performance additives for materials. Owing to its relative stability and the distinctive mass spectral features of hindered enones, it is also useful as a reference/standard for analytical method development (GC/MS, LC/MS) and for kinetic studies of reactions involving congested enones.

  • Solubility @25˚C

    Solvent Solubility (g/L)
    ethanol 658.12
    methanol 701.22
    isopropanol 693.33
    water 5.58
    ethyl acetate 790.64
    n-propanol 637.34
    acetone 675.6
    n-butanol 538.69
    acetonitrile 714.59
    DMF 874.09
    toluene 481.55
    isobutanol 477.55
    1,4-dioxane 1289.33
    methyl acetate 755.26
    THF 1411.29
    2-butanone 771.76
    n-pentanol 321.18
    sec-butanol 555.43
    n-hexane 120.03
    ethylene glycol 148.3
    NMP 494.76
    cyclohexane 130.29
    DMSO 432.17
    n-butyl acetate 489.29
    n-octanol 319.93
    chloroform 1432.38
    n-propyl acetate 331.79
    acetic acid 293.33
    dichloromethane 1101.41
    cyclohexanone 724.25
    propylene glycol 221.67
    isopropyl acetate 472.17
    DMAc 595.8
    2-ethoxyethanol 416.32
    isopentanol 448.32
    n-heptane 82.91
    ethyl formate 378.24
    1,2-dichloroethane 703.01
    n-hexanol 638.21
    2-methoxyethanol 674.45
    isobutyl acetate 241.23
    tetrachloromethane 365.86
    n-pentyl acetate 326.96
    transcutol 1096.79
    n-heptanol 325.14
    ethylbenzene 288.03
    MIBK 395.82
    2-propoxyethanol 818.15
    tert-butanol 701.15
    MTBE 699.62
    2-butoxyethanol 448.39
    propionic acid 400.48
    o-xylene 298.73
    formic acid 129.56
    diethyl ether 699.81
    m-xylene 360.59
    p-xylene 393.24
    chlorobenzene 509.9
    dimethyl carbonate 241.02
    n-octane 46.29
    formamide 201.42
    cyclopentanone 833.74
    2-pentanone 589.87
    anisole 519.43
    cyclopentyl methyl ether 619.11
    gamma-butyrolactone 814.55
    1-methoxy-2-propanol 664.97
    pyridine 714.48
    3-pentanone 484.34
    furfural 657.12
    n-dodecane 36.31
    diethylene glycol 452.88
    diisopropyl ether 258.95
    tert-amyl alcohol 531.11
    acetylacetone 559.4
    n-hexadecane 42.03
    acetophenone 364.78
    methyl propionate 572.19
    isopentyl acetate 436.33
    trichloroethylene 1177.14
    n-nonanol 272.64
    cyclohexanol 426.65
    benzyl alcohol 321.02
    2-ethylhexanol 325.18
    isooctanol 258.28
    dipropyl ether 347.06
    1,2-dichlorobenzene 436.42
    ethyl lactate 181.4
    propylene carbonate 458.99
    n-methylformamide 451.48
    2-pentanol 438.07
    n-pentane 112.05
    1-propoxy-2-propanol 583.23
    1-methoxy-2-propyl acetate 508.17
    2-(2-methoxypropoxy) propanol 338.04
    mesitylene 246.63
    ε-caprolactone 613.01
    p-cymene 178.47
    epichlorohydrin 951.42
    1,1,1-trichloroethane 952.53
    2-aminoethanol 322.32
    morpholine-4-carbaldehyde 759.55
    sulfolane 610.02
    2,2,4-trimethylpentane 61.7
    2-methyltetrahydrofuran 845.4
    n-hexyl acetate 489.56
    isooctane 63.82
    2-(2-butoxyethoxy)ethanol 483.56
    sec-butyl acetate 283.83
    tert-butyl acetate 468.02
    decalin 93.1
    glycerin 232.55
    diglyme 796.12
    acrylic acid 297.29
    isopropyl myristate 184.53
    n-butyric acid 504.22
    acetyl acetate 401.33
    di(2-ethylhexyl) phthalate 148.07
    ethyl propionate 347.26
    nitromethane 619.85
    1,2-diethoxyethane 498.14
    benzonitrile 442.17
    trioctyl phosphate 120.26
    1-bromopropane 559.05
    gamma-valerolactone 983.04
    n-decanol 199.47
    triethyl phosphate 149.32
    4-methyl-2-pentanol 288.27
    propionitrile 648.23
    vinylene carbonate 433.11
    1,1,2-trichlorotrifluoroethane 507.13
    DMS 358.15
    cumene 214.97
    2-octanol 241.73
    2-hexanone 380.06
    octyl acetate 236.47
    limonene 224.81
    1,2-dimethoxyethane 674.1
    ethyl orthosilicate 154.42
    tributyl phosphate 136.37
    diacetone alcohol 480.54
    N,N-dimethylaniline 325.98
    acrylonitrile 669.52
    aniline 462.37
    1,3-propanediol 396.0
    bromobenzene 529.32
    dibromomethane 785.28
    1,1,2,2-tetrachloroethane 933.34
    2-methyl-cyclohexyl acetate 250.62
    tetrabutyl urea 163.84
    diisobutyl methanol 196.94
    2-phenylethanol 440.57
    styrene 312.3
    dioctyl adipate 200.4
    dimethyl sulfate 298.58
    ethyl butyrate 323.57
    methyl lactate 245.55
    butyl lactate 232.74
    diethyl carbonate 212.77
    propanediol butyl ether 359.66
    triethyl orthoformate 221.25
    p-tert-butyltoluene 196.62
    methyl 4-tert-butylbenzoate 349.02
    morpholine 1215.05
    tert-butylamine 492.35
    n-dodecanol 150.46
    dimethoxymethane 614.43
    ethylene carbonate 367.77
    cyrene 263.9
    2-ethoxyethyl acetate 422.29
    2-ethylhexyl acetate 338.66
    1,2,4-trichlorobenzene 466.47
    4-methylpyridine 770.38
    dibutyl ether 297.96
    2,6-dimethyl-4-heptanol 196.94
    DEF 512.56
    dimethyl isosorbide 507.23
    tetrachloroethylene 610.13
    eugenol 333.7
    triacetin 313.79
    span 80 308.07
    1,4-butanediol 160.2
    1,1-dichloroethane 951.84
    2-methyl-1-pentanol 280.53
    methyl formate 352.23
    2-methyl-1-butanol 417.82
    n-decane 63.47
    butyronitrile 598.15
    3,7-dimethyl-1-octanol 283.81
    1-chlorooctane 219.8
    1-chlorotetradecane 91.2
    n-nonane 61.47
    undecane 46.45
    tert-butylcyclohexane 99.14
    cyclooctane 61.6
    cyclopentanol 456.04
    tetrahydropyran 975.78
    tert-amyl methyl ether 454.57
    2,5,8-trioxanonane 468.16
    1-hexene 322.01
    2-isopropoxyethanol 349.45
    2,2,2-trifluoroethanol 184.68
    methyl butyrate 381.8

    Scent© AI

1 3

IFRA standard 51

Recommendation
No restriction
Maximum acceptable concentrations in the finished product (%)
Category 1
Products applied to the lips
 No restriction Category 7A
Rinse-off products applied to the hair with some hand contact
 No restriction
Category 2
Products applied to the axillae
 No restriction Category 7B
Leave-on products applied to the hair with some hand contact
 No restriction
Category 3
Products applied to the face/body using fingertips
 No restriction Category 8
Products with significant anogenital exposure
 No restriction
Category 4
Products related to fine fragrance
 No restriction Category 9
Products with body and hand exposure, primarily rinse off
 No restriction
Category 5A
Body lotion products applied to the body using the hands (palms), primarily leave on
 No restriction Category 10A
Household care products with mostly hand contact
 No restriction
Category 5B
Face moisturizer products applied to the face using the hands (palms), primarily leave on
 No restriction Category 10B
Household care products with mostly hand contact, including aerosol/spray products (with potential leave-on skin contact)
 No restriction
Category 5C
Hand cream products applied to the hands using the hands (palms), primarily leave on
 No restriction Category 11A
Products with intended skin contact but minimal transfer of fragrance to skin from inert substrate without UV exposure
 No restriction
Category 5D
Baby Creams, baby Oils and baby talc
 No restriction Category 11B
Products with intended skin contact but minimal transfer of fragrance to skin from inert substrate with potential UV exposure
 No restriction
Category 6
Products with oral and lip exposure
 No restriction Category 12
Products not intended for direct skin contact, minimal or insignificant transfer to skin
 No restriction

Botanical

Name CAS Botanical Proportion
Orris butter 8002-73-1 Iris florentina L., fam. Iridaceae 0.01%
Saffron 2 8022-19-3 Crocus sativus L., fam. Iridaceae 0.95%